Reagent-Free Esterification from Benzoyl Hydrazines and Alcohols under Electrochemical Conditions

Abstract

A scalable electrochemical esterification between aroylhydrazides and alcohols to give structurally versatile carboxylic esters was developed. This strategy features mild reaction conditions and a relatively broad substrate scope with good functional group compatibility. In addition, the transformation is operationally simple and free from external oxidants and mediating chemical reagents.

Key words

electrochemical synthesis - esterification - aroylhydrazides - reagent-free reaction - anode oxidation

Publikationsverlauf

Eingereicht: 19. Dezember 2022

Angenommen nach Revision: 28. Februar 2023

Accepted Manuscript online:
28. Februar 2023

Artikel online veröffentlicht:
09. Mai 2023

• References

• 1a Ishihara K, Ohara S, Yamamoto H. Science 2000; 290: 1140
• 1b Carboxylic Acid Derivatives Synthesis. In Name Reactions for Functional Group Transformations. Li JJ, Corey EJ. John Wiley & Sons, Inc; Hoboken: 2007
• 1c Ganesh M, Saroj KR, Suresh R, Srimanta G, Bhisma KP. Org. Biomol. Chem. 2016; 14: 8178
• 2a Brown R, Quirk J, Kirkpatrick P. Nat. Rev. Drug Discovery 2003; 2: 177
• 2b Klumpp K, Smith DB. Discovery and Clinical Evaluation of the Nucleoside Analog Balapiravir (R1626) for the Treatment of HCV Infection. In Antiviral Drugs: From Basic Discovery Through Clinical Trials, 1st ed. Kazmierski WM. Wiley; New York: 2011: 287-304
• 3a Munday RH, Martinelli JR, Buchwald SL. J. Am. Chem. Soc. 2008; 130: 2754
• 3b Shang R, Fu Y, Li J.-B, Zhang S.-L, Guo Q.-X, Liu L. J. Am. Chem. Soc. 2009; 131: 5738
• 3c Liang A, Han S, Wang L, Li J, Zou D, Wu Y, Wu Y. Adv. Synth. Catal. 2015; 357: 3104
• 3d Hie L, Fine Nathel NF, Shah TK, Baker EL, Hong X, Yang Y.-F, Liu P, Houk KN, Garg NK. Nature 2015; 524: 79
• 4a Gopinath R, Patel BK. Org. Lett. 2000; 2: 577
• 4b Maji B, Vedachalan S, Ge X, Cai S, Liu X.-W. J. Org. Chem. 2011; 76: 3016
• 4c Liu C, Tang S, Zheng L, Liu D, Zhang H, Lei A. Angew. Chem. Int. Ed. 2012; 51: 5662
• 4d Miyamura H, Kobayashi S. Acc. Chem. Res. 2014; 47: 1054
• 4e Gaspa S, Porcheddu A, De Luca L. Org. Lett. 2015; 17: 3666
• 4f Whittaker AM, Dong VM. Angew. Chem. Int. Ed. 2015; 54: 1312
• 4g Cheng J, Zhu M, Wang C, Li J, Jiang X, Wei Y, Tang W, Xue D, Xiao J. Chem. Sci. 2016; 7: 4428
• 4h Su H, Zhang K.-X, Zhang B, Wang H.-H, Yu Q.-Y, Li X.-H, Antonietti M, Chen J.-S. J. Am. Chem. Soc. 2017; 139: 811
• 4i Yu H, Wang J, Wu Z, Zhao Q, Dan D, Han S, Tang J, Wei Y. Green Chem. 2019; 21: 4550
• 4j Das UK, Ben-David Y, Leitus G, Diskin-Posner Y, Milstein D. ACS Catal. 2019; 9: 479
• 5a Liu H, Chen G, Jiang H, Li Y, Luque R. ChemSusChem 2012; 5: 1892
• 5b Liu M, Chen T, Yin S.-F. Catal. Sci. Technol. 2016; 6: 690
• 6a Little RD, Moeller KD. Electrochem. Soc. Interface 2002; 11: 36
• 6b Lorion MM, Maindan K, Kapdi AR, Ackermann L. Chem. Soc. Rev. 2017; 46: 7399
• 6c Jiang Y, Xu K, Zeng C. Chem. Rev. 2018; 118: 4485
• 6d Tang S, Liu Y, Lei A. Chem 2018; 4: 27
• 6e Chen N, Xu HC. Chem. Rec. 2021; 21: 2306
• 6f Wang X.-Y, Zhong Y.-F, Mo Z.-Y, Wu S.-H, Xu Y.-L, Tang H.-T, Pan Y.-M. Adv. Synth. Catal. 2021; 363: 208
• 7 Yu C, Özkaya B, Patureau FW. Chem. Eur. J. 2021; 27: 3682
• 8 Subramanian K, Yedage SL, Bhanage BM. J. Org. Chem. 2017; 82: 10025
• 9a Finney EE, Ogawa KA, Boydston AJ. J. Am. Chem. Soc. 2012; 134: 12374
• 9b Smeyne D, Verboom K, Bryan M, LoBue J, Shaikh A. Tetrahedron Lett. 2021; 68: 152898
• 9c Hou Z.-W, Zhang M.-M, Yang W.-C, Wang L. J. Org. Chem. 2022; 87: 7806
• 10a Braslau R, Anderson MO, Rivera F, Jimenez A, Haddad T, Axon JR. Tetrahedron 2002; 58: 5513
• 10b Xie S, Su L, Mo M, Zhou W, Zhou Y, Dong J. J. Org. Chem. 2021; 86: 739
• 10c Wang S.-N, Zhang G.-Y, Shoberu A, Zou J.-P. J. Org. Chem. 2021; 86: 9067
• 10d Wang Y.-J, Zhang G.-Y, Shoberu A, Zou J.-P. Tetrahedron Lett. 2021; 80: 153316
• 11 Alam T, Rakshit A, Nath Dhara H, Palai A, Patel BK. Org. Lett. 2022; 24: 6619
• 12 Zhang H, Wang T, Xu K, Zeng C. J. Org. Chem. 2021; 86: 16171
• 13a Ning Z, Zhang Z, Yan Q, Zhou N, Wen L, Peng X, Tang Y, Feng P. Sci. China: Chem. 2022; 65: 1962
• 13b Ruan Z, Huang Z, Xu Z, Zeng S, Feng P, Sun P.-H. Sci. China: Chem. 2021; 64: 800
• 13c Peng X, Zhao J, Ma G, Wu Y, Hu S, Ruan Z, Feng P. Green Chem. 2021; 23: 8853
• 14 Wu J, Zhou Y, Zhou Y, Chiang C.-W, Lei A. ACS Catal. 2017; 7: 8320
• 15a Yamaguchi J.-i, Aoyagi T, Fujikura R, Suyama T. Chem. Lett. 2001; 466
• 15b Cheng S.-Y, Ou C.-H, Lin H.-M, Jia J.-S, Tang H.-T, Pan Y.-M, Huang G.-B, Meng X.-J. Chin. J. Org. Chem. 2021; 41: 4718
• 16 Yao M.-L, Reddy MS, Yong L, Walfish I, Blevins DW, Kabalka GW. Org. Lett. 2010; 12: 700
• 17 Padala AK, Saikam V, Ali A, Ahmed QN. Tetrahedron 2015; 71: 9380
• 18 Nishii Y, Hirai T, Fernandez S, Knochel P, Mashima K. Eur. J. Org. Chem. 2017; 5010
• 19 Majek M, von Wangelin AJ. Angew. Chem. Int. Ed. 2014; 53: 2270
• 20 Luo H, Yang Y, Yang B, Xu ZJ, Wang D. J. Chem. Res. 2021; 45: 649
• 21 Liu B, Elder WZ, Miyake GM. J. Org. Chem. 2020; 85: 3717
• 22 Kleinpeter E, Werner P, Linker T. Tetrahedron 2017; 73: 3801
• 23 Zhu Y, Wei YY. Eur. J. Org. Chem. 2013; 4503
• 24 Panchan W, Chiampanichayakul S, Snyder DL, Yodbuntung S, Pohmakotr M, Reutrakul V, Jaipetch T, Kuhakarn C. Tetrahedron 2010; 66: 2732
• 25 Raj IV. P, Sudalai A. Tetrahedron Lett. 2005; 46: 8303
• 26 Slagman S, Escorihuela J, Zuilhof H, Franssen MC. R. RSC Adv. 2016; 6: 99367
• 27 Rajabi F, Arancon RA. D, Luque R. Catal. Commun. 2015; 59: 101
• 28 Wang LY, Li J, Dai W, Lv Y, Zhang Y, Gao S. Green Chem. 2014; 16: 2164
• 29 Rammurthy B, Peraka S, Vasu A, Sai GK, Rohini YD, Narender N. Asian J. Org. Chem. 2021; 10: 594
• 30 Jang M, Lim T, Park BY, Han MS. J. Org. Chem. 2022; 87: 910
• 31 Meng H, Gao S, Luo M, Zeng XM. Eur. J. Org. Chem. 2019; 4617
• 32 Kisic A, Stephan M, Mohar B. Org. Lett. 2013; 15: 1614